Agricultural agent containing 2,5-diketopiperazine derivative as active ingredient

Abstract

Disclosed herein is an agricultural agent containing a 2,5-diketopiperazine derivative capable of controlling plant diseases and promoting plant growth or an agriculturally acceptable salt thereof as an active ingredient.

1 . An agricultural agent comprising a compound selected from a 2,5-diketopiperazine derivative represented by Chemical Formula 1 and an agriculturally acceptable salt thereof as an active ingredient: 
       
         
           
           
               
               
           
         
         where 
         each of R 1  and R 6  is a hydrogen atom; 
         each of R 2 , R 3 , R 4  and R 5 , which are identical or different, is a hydrogen atom or a C 1 -C 6  linear or branched alkyl group substituted or unsubstituted with a substituent selected from hydroxy, mercapto, amino, guanidino, carbamoyl, carboxyl, C 1 -C 6  alkoxycarbonyl, C 1 -C 6  alkylthio, tritylthio, acetylamine, phenyl, hydroxyphenyl, imidazolyl and indolyl, 
         wherein one of R 2  and R 3  may be linked with R 1  to form a 5- to 7-membered fused ring or one of R 4  and R 5  may be linked with R 6  to form a 5- to 7-membered fused ring. 
       
     
     
         2 . The agricultural agent according to  claim 1 , wherein the 2,5-diketopiperazine derivative represented by Chemical Formula 1 is a racemate or an isomer. 
     
     
         3 . The agricultural agent according to  claim 1 , wherein
 each of R 1  and R 6  is a hydrogen atom;   each of R 2 , R 3 , R 4  and R 5 , which are identical or different, is a hydrogen atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a 2-methylethyl group, a 1-methylpropyl group, a 2-methylpropyl group, a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, an imidazol-4-yl-methyl group, a 2-methylthioethyl group, a benzyl group, a 4-hydroxybenzyl group, a phenethyl group, a mercaptomethyl group, a methylthiomethyl group, a 2-methylthioethyl group, a tritylthiomethyl group, a 2-tritylthioethyl group, a 2-ethoxycarbonylethyl group, a 2-methoxycarbonylethyl group, a rnethoxycarbonylmethyl group, a 2-methoxycarbonylethyl group, an ethoxycarbonylmethyl group, a 2-aminoethyl group, a carbamoylmethyl group, a 2-carbamoylethyl group, an acetylaminomethyl group, a 2-acetylaminoethyl group, a carboxymethyl group, a 2-carboxyethyl group, an imidazol-4-ylmethyl group, a 2-(imidazol-4-yl)thyl group, a 3-guanidinopropyl, an indol-3-ylmethyl group or a 2-(indol-3-yl)ethyl group,   wherein one of R 2  and R 3  is linked to R 1  via —(CH 2 ) 3 — to form a 5-membered ring or one of R 4  and R 5  is linked to R 6  via —(CH 2 ) 3 — to form a 5-membered ring.   
     
     
         4 . The agricultural agent according to  claim 1 , which comprises a 2,5-diketopiperazine compound selected from the followings or an agriculturally acceptable salt thereof as an active ingredient:
 3-hydroxymethyl-6-(2-methylpropyl)-2,5-diketopiperazine,   3-(2-methylpropyl)-2,5-diketopiperazine,   3-(1-hydroxyethyl)-6-(2-methylpropyl)-2,5-diketopiperazine,   3-isopropyl-2,5-diketopiperazine,   3-(indol-3-ylmethyl)-2,5-diketopiperazine,   2,5-diketopiperazine,   3-methyl-2,5-diketopiperazine,   3,6-dimethyl-2,5-diketopiperazine,   3-methyl-6-(2-methylethyl)-2,5-diketopiperazine,   3-methyl-6-(4-hydroxybenzyl)-2,5-diketopiperazine,   3-(1-hydroxyethyl)-6-(2-mercaptomethyl)-2,5-diketopiperazine,   3-(1-hydroxyethyl)-6-(2-methylthiomethyl)-2,5-diketopiperazine,   3-(1-hydroxyethyl)-6-(2-tritylthiomethyl)-2,5-diketopiperazine,   3-(1-hydroxyethyl)-6-benzyl-2,5-diketopiperazine,   3-(1-hydroxyethyl)-6-(4-hydroxybenzyl)-2,5-diketopiperazine,   3-(1-hydroxyethyl)-6-(indol-3-ylmethyl)-2,5-diketopiperazine,   3-(2-methylpropyl)-6-(2-mercaptomethyl)-2,5-diketopiperazine,   3-(2-methylpropyl)-6-(2-methylthiomethyl)-2,5-diketopiperazine,   3-(2-methylpropyl)-6-(2-tritylthiomethyl)-2,5-diketopiperazine,   3-(2-methylpropyl)-6-benzyl-2,5-diketopiperazine,   3-(2-methylpropyl)-6-(4-hydroxybenzyl)-2,5-diketopiperazine,   3-(2-methylpropyl)-6-(indol-3-ylmethyl)-2,5-diketopiperazine,   3-(4-hydroxybenzyl)hexahydropyrrolo[1,2-a]pyrazin-1,4-dione,   3-benzylhexahydropyrrolo[1,2-a]pyrazin-1,4-dione,   3-methylhexahydropyrrolo[1,2-a]pyrazin-1,4-dione,   3-isopropylhexahydropyrrolo[1,2-a]pyrazin-1,4-dione,   3-(2-methylpropyl)hexahydropyrrolo[1,2-a]pyrazin-1,4-dione,   3-(1-methylpropyl)hexahydropyrrolo[1,2-a]pyrazin-1,4-dione,   hexahydropyrrolo[1,2-a]pyrazin-1,4-dione,   3-(indol-3-ylmethyl)hexahydropyrrolo[1,2-a]pyrazin-1,4-dione,   octahydropyrrolo[1,2-a:1′,2′-d]pyrazin-5,10-dione,   3-hydroxymethylhexahydropyrrolo[1,2-a]pyrazin-1,4-dione,   3-(1-hydroxyethyl)hexahydropyrrolo[1,2-a]pyrazin-1,4-dione,   3-benzylhexahydropyrrolo[1,2-a]pyrazin-1,4-dione,   3-(4-hydroxybenzyl)hexahydropyrrolo[1,2-a]pyrazin-1,4-dione,   3-benzylhexahydropyrrolo[1,2-a]pyrazin-1,4-dione,   3-(2-carbamoylethyl)hexahydropyrrolo[1,2-a]pyrazin-1,4-dione,   3-(2-methylthioethyl)hexahydropyrrolo[1,2-a]pyrazin-1,4-dione,   3-carbamoylmethylhexahydropyrrolo[1,2-a]pyrazin-1,4-dione,   3-mercaptomethylhexahydropyrrlolo[1,2-a]pyrazin-1,4-dione,   3-methylthiomethylhexahydropyrrolo[1,2-a]pyrazin-1,4-dione,   3-tritylthiomethylhexahydropyrrolo[1,2-a]pyrazin-1,4-dione,   3-(2-methoxycarbonylethyl)hexahydropyrrolo[1,2-a]pyrazin-1,4-dione,   3-(2-methoxycarbonylmethyl)hexahydropyrrolo[1,2-a]pyrazin-1,4-dione,   3-(2-aminoethyl)hexahydropyrrolo[1,2-a]pyrazin-1,4-dione,   3-(2-carboxyethyl)hexahydropyrrolo[1,2-a]pyrazin-1,4-dione,   3-(2-carboxymethyl)hexahydropyrrolo[1,2-a]pyrazin-1,4-dione,   3-(imidazol-4-ylmethyl)hexahydropyrrolo[1,2-a]pyrazin-1,4-dione and   3-(2-acetylaminoethyl)hexahydropyrrolo[1,2-a]pyrazin-1,4-dione.   
     
     
         5 . The agricultural agent according to  claim 1 , which further comprises one or more selected from a microbicide, an insecticide, a herbicide, a plant growth regulator and a fertilizer as an active ingredient. 
     
     
         6 . The agricultural agent according to  claim 1 , which is formulated into a wettable powder, a suspension, an emulsifiable concentrate, an emulsion, a microemulsion, a soluble concentrate, a dispersible concentrate, a water-dispersible granule, a granule, a dustable powder, a suspendable concentrate, a water-dispersible granule, a floating granule or a tablet. 
     
     
         7 . The agricultural agent according to  claim 1 , which promotes plant growth, provides induced systemic resistance (ISR) against plant diseases or both. 
     
     
         8 . The agricultural agent according to  claim 7 , wherein the plant disease is soft rot, damping off, blight, withering, spot or mosaic disease. 
     
     
         9 . The agricultural agent according to  claim 7 , wherein the plant is a dicotyledon. 
     
     
         10 . The agricultural agent according to  claim 9 , wherein the dicotyledon is selected from tobacco, Chinese cabbage, red pepper, cucumber, potato and tomato. 
     
     
         11 . A method for promoting plant growth, comprising treating a plant with the agricultural agent according to  claim 1 . 
     
     
         12 . The method for promoting plant growth according to  claim 11 , wherein the plant is a dicotyledon. 
     
     
         13 . The method for promoting plant growth according to  claim 12 , wherein the dicotyledon is selected from tobacco, Chinese cabbage, red pepper, cucumber, potato and tomato. 
     
     
         14 . A method for preventing or inhibiting a plant disease, comprising treating a plant with the agricultural agent according to  claim 1 . 
     
     
         15 . The method for preventing or inhibiting a plant disease according to  claim 14 , wherein the plant is a dicotyledon. 
     
     
         16 . The method for preventing or inhibiting a plant disease according to  claim 15 , wherein the dicotyledon is selected from tobacco, Chinese cabbage, red pepper, cucumber, potato and tomato. 
     
     
         17 . The method for preventing or inhibiting a plant disease according to  claim 14 , wherein the plant disease is soft rot, damping off, blight, withering, spot or mosaic disease.